Zhang Zichun, Li Yuanhe, Zhao Dandan, He Yingdong, Gong Jianxian, Yang Zhen
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering.
Chemistry. 2017 Jan 26;23(6):1258-1262. doi: 10.1002/chem.201605438. Epub 2017 Jan 3.
The synthesis of strained polycyclic systems from readily available precursors with a minimum number of steps and with regio- and stereochemical control constitutes an important synthetic challenge. Herein, we report a tandem reaction comprising Co-TMTU (tetramethyl thiourea)-catalyzed Pauson-Khand (PK) and 6π-electrocyclization reactions for the formation of the highly strained core of presilphiperfolanols. The developed chemistry has been applied to the total syntheses of 4-epi-presilphiperfolan-8-ol and 7-epi-presilphiperfolan-1-ol.
从容易获得的前体出发，通过最少的步骤并实现区域和立体化学控制来合成张力多环体系，是一项重要的合成挑战。在此，我们报道了一种串联反应，该反应由钴-四甲基硫脲（Co-TMTU）催化的Pauson-Khand（PK）反应和6π-电环化反应组成，用于形成前硅石蒜醇的高张力核心。所开发的化学方法已应用于4-表-前硅石蒜醇-8-醇和7-表-前硅石蒜醇-1-醇的全合成。
